In
a continuous study on the high-value-added exploration of a
renewable forest bioresource turpentine in modern organic agriculture,
two series of α-pinene derivatives containing amide and α,β-unsaturated
ketone pharmacophores were prepared. Through an in-depth fungicidal
activity study, the title compounds presented excellent inhibitory
activity against common crop fungi, especially Sclerotinia
sclerotiorum, and the notable EC50 values
of α,β-unsaturated compounds 3u (funan containing) and
3v (thiophene containing) were 1.657 and 1.749 μg/mL, respectively.
Further physiological and biochemical studies on S.
sclerotiorum revealed that compounds 3u and 3v reduced
the ergosterol content in the cell membrane and increased the permeability
of the cell membrane. In combination with their effect on mycelial
morphology, the title compounds might have inhibitory effects on the
biosynthesis of ergosterol, which is a paramount component of the
target cell membrane. Moreover, quantitative structure–activity
relationship (QSAR) and SAR studies revealed that the charge distribution
of α,β-unsaturated carbonyl ketone derivatives played
an important role in the observed fungicidal activity. In summary,
this study highlights the design and development of novel high-efficacy
turpentine-based antifungal agents.
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